Highly recommend you looking into a checkbook IRA instead of cashing out.Sure you can take out the principle since you’ve already paid taxes on it but this money is supposed to be for your retirement and in a Roth your real estate can grow tax free, though check with a CPA to see if STR will trigger UBIT in an IRA.

Once you find a good property and all the numbers make sense - pull the trigger.

So brainstorm the different options then pull the trigger!

What has kept you from pulling the trigger thus far?

This allows you to use the funds without triggering penalties or taxes, as long as you stick to the repayment schedule.These strategies all come with rules and limitations, so it’s a good idea to check with a tax advisor before moving forward. 

One of the other factors that kept me from pulling the trigger is that the city has never passed any real STR regulation.

It may trigger if you are paying down the balance aggressively during the prepayment penalty period. 

I would love to get a condo down in Miami to have a as a forever rental, but it's just so hard for me to pull the trigger.

I used sankeymatic.com after a bunch of massaging of the numbers in a spreadsheet. 

I will definitely try to bring in as much money as possible but I don't want to wait forever to pull the trigger.